Process of manufacturing substituted secondary amines of the benzylanilid type



Patented Mar. 28, 1933 UNITED STATES WILHELM HERZBERG, or BERLIN-WILMEBSDORF, ND nANs nat on, or" BERLIN FRIEDENAU, GERMANY, ASSIGNORS, BY EsNn ASSIGNMENTS, T wm'rnnor CHEMICAL C'OMIANY, INC., on NEW YORK, n. Y., A conronnrrolvor NEW onx PROCESS OF MANUFACTURING SUBSTITUTED SECONDARY AMINES OF THE BENZYL- ANILID TYPE No Drawing. Application filed April 13, 1926, Serial No. 101,792, and in Germany April 15, 192

This invention relates to the manufacture of substituted secondary amines of the benzyl-anilid type by the reaction of an aralkylamine with a halogenaryl-compound, in

5 which the halogen is easily exchanged, for instance with dinitrochlorobenzene, Q-nitrol-chlorobenzene-4-sulfonic acid, i-nitro-lchlorobenzene-2-sulfonic acid, in accordance with the equation:

hydrous sodium carbonate are added and the Ewample 2.173 parts'of the hydrochloride of 4-methoxybenzylamine (anisamine) and 260 parts of sodium' 2-nitro-1-chlorobenzene-L-sulfonate are dissolved in. water, and, after addition of 106 parts of anhydrous sodium carbonate, the whole is boiled in a reflux apparatus for 2-3 hours. On cooling and salting out sodium-lnnethoxyl-benzylamino-2-nitrobenzene-4-sulfonate in yellow crystals.

Ewa'mple 3.95 parts of vanillylamine hydrochloride, 160 parts of potassium-2.6-dinitro-1-ohlorobenzene-4-sulfonate and parts of potassium carbonate are dissolved in water. While stirring, a further 35 parts of potassium carbonate are added gradually. The decomposition oocursin the cold and may be completed by warming for ashort time. crystals of potassium 4L hydroxy 3'- methoxy-l-benzylamino 2.6-dinitrobenzene- -sulfonate.

The reaction which represented .as follows 09 whole is boiled in a reflux apparatus for 23 hours. On cooling, yellow crystals of sodium-2.4-dimethyl l-benzylaminoi-nitrobenzene-2-sulfonate separate, the separation 40 being completed by adding common salt.

The reaction which takes place may be rep resented as follows:

-' Example 4.192 parts of 4-methyl-3 chloseparates There are obtained orange colored 70 7 takes place may, be

- I vs PATENT emu robenzylamine hydrochloride and 260 parts of sodium 4 nitro 1 chlorobenzene-Q-sulfonate are dissolved in water, 106 parts of an: hydrous sodium carbonate are added and the whole is boiled ina reflux apparatusvfor a few hours. On cooling, sodiuml methyl i f chloro 1 benzylamino-4-nitrobenzene-2-sulfonate separates in yellow crystals.

Est-ample 5.-157 parts of phenylethylamine hydrochloride and 260 parts. of so- 5 dium-4-nitro-l-chlorobenzene-2-sulfonate are dissolved in water. 106 parts of anhydrous sodium carbonate are added and the whole is boiled for 23 hours in a reflux apparatus. Sodium 1 (phenylethylamino) 4- nitroben Q zene-Q-sulfonate separates. v

Ewam-ple 6.157 parts of C-l-naphthylmethylamine 260 parts of s'odium--nitrol-chlorobenzene-Q-sulfonate and 53 parts of anhydrous sodium carbonate are dissolved in water and the solution is boiled in a reflux apparatus for a few hours; after cooling, there separates a yellow crystalline mass of sodium C 1 naphthyl 1 '1 methylamino-l-nitrobenzene-Q-sulfonate.

The reaction which takes place may be represented as follows:

8OHFNH ONO2+NaHC/Oz+NaG I NaOaS What we claim is:

-1. The process which comprises reacting on a primary aralkylamine with a nitrochlor benzene compound in which the chlorine is easily exchanged, in an'aqueous solution and in the presence of an alkali at a temperature not exceeding the boiling point.

2. The process which comprises reacting on vanillyl amine with an alkali metal salt of 2.6di11it10-1-ChlOIOlOBDZGIlB-l-SlllfOIliC acid in an aqueous solution and in the presence of an alkali at a temperature not exceeding the boiling point. 7 e V 3. The process which comprises reacting on a primary'aralkylamine'with a mono chlor-dinitro benzene compound in which the chlorine is easily exchanged in an aqueous solution and in the presence of an alkali at a temperature not exceeding the boiling point. v I

" 4. The process which comprises reacting on a primary aralkylamine with an'alkali metal salt of a ,nitrochlor benzene sulfonic acid, in an aqueous solution and in the presence of an alkali at a temperature not exceeding the boiling point. e V In testimony whereof we aflix our signa m WILHELM HERZBERG.

' HANS LANGE. 

